DE2920591C2 - - Google Patents
Info
- Publication number
- DE2920591C2 DE2920591C2 DE2920591A DE2920591A DE2920591C2 DE 2920591 C2 DE2920591 C2 DE 2920591C2 DE 2920591 A DE2920591 A DE 2920591A DE 2920591 A DE2920591 A DE 2920591A DE 2920591 C2 DE2920591 C2 DE 2920591C2
- Authority
- DE
- Germany
- Prior art keywords
- bromine
- amount
- chlorine
- alkali metal
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- 150000008282 halocarbons Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 8
- 150000008045 alkali metal halides Chemical class 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000003880 polar aprotic solvent Substances 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- GSSNCQXGQSCKSL-UHFFFAOYSA-N 2-chloro-1,1,1-trifluoro-5-methylhexa-2,4-diene Chemical compound CC(C)=CC=C(Cl)C(F)(F)F GSSNCQXGQSCKSL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- JRAGTVVQLNANCA-UHFFFAOYSA-N 5,5-dichloro-6,6,6-trifluoro-2-methylhex-2-ene Chemical compound CC(C)=CCC(Cl)(Cl)C(F)(F)F JRAGTVVQLNANCA-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- JXOGUSUARSCHAD-UHFFFAOYSA-N 2,2,4-trichloro-1,1,1-trifluoro-5-methylhexane Chemical compound CC(C)C(Cl)CC(Cl)(Cl)C(F)(F)F JXOGUSUARSCHAD-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical class CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- AFVLVVWMAFSXCK-VMPITWQZSA-N alpha-cyano-4-hydroxycinnamic acid Chemical class OC(=O)C(\C#N)=C\C1=CC=C(O)C=C1 AFVLVVWMAFSXCK-VMPITWQZSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- -1 α- ethynyl Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/19—Halogenated dienes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2242978 | 1978-05-25 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2920591A1 DE2920591A1 (de) | 1979-11-29 |
| DE2920591C2 true DE2920591C2 (enrdf_load_stackoverflow) | 1989-11-16 |
Family
ID=10179232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792920591 Granted DE2920591A1 (de) | 1978-05-25 | 1979-05-21 | Halogenierte kohlenwasserstoffe und verfahren zu ihrer herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4210611A (enrdf_load_stackoverflow) |
| JP (2) | JPS54163506A (enrdf_load_stackoverflow) |
| CH (1) | CH642041A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2920591A1 (enrdf_load_stackoverflow) |
| DK (1) | DK213479A (enrdf_load_stackoverflow) |
| FR (1) | FR2426665A1 (enrdf_load_stackoverflow) |
| IT (1) | IT1115235B (enrdf_load_stackoverflow) |
| NL (1) | NL7904057A (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228107A (en) * | 1978-05-25 | 1980-10-14 | Imperial Chemical Industries Limited | Polyhalogenated hydrocarbons, useful as insecticide intermediates, and methods for their preparation |
| DE2835480A1 (de) * | 1978-08-12 | 1980-02-28 | Hoechst Ag | Fluorhaltige 1.3-diene, deren herstellung und deren verwendung |
| DE3061592D1 (en) * | 1979-07-13 | 1983-02-17 | Ici Plc | Process for the manufacture of halogenated hydrocarbons |
| ZA849230B (en) * | 1983-12-07 | 1985-07-31 | Fmc Corp | Biocidal fluoroalkanes and fluoroalkenes |
| US8530708B2 (en) * | 2003-07-25 | 2013-09-10 | Honeywell International Inc. | Processes for selective dehydrohalogenation of halogenated alkanes |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3925491A (en) * | 1973-02-28 | 1975-12-09 | Ugine Kuhlmann | New fluorinated dienes and process for preparing same |
| DE2963946D1 (en) * | 1978-10-26 | 1982-12-02 | Ici Plc | Halogenated hydrocarbons and a method for their preparation |
-
1979
- 1979-05-18 US US06/040,455 patent/US4210611A/en not_active Expired - Lifetime
- 1979-05-21 DE DE19792920591 patent/DE2920591A1/de active Granted
- 1979-05-22 CH CH480179A patent/CH642041A5/de not_active IP Right Cessation
- 1979-05-23 DK DK213479A patent/DK213479A/da unknown
- 1979-05-23 NL NL7904057A patent/NL7904057A/xx not_active Application Discontinuation
- 1979-05-23 IT IT22924/79A patent/IT1115235B/it active
- 1979-05-23 FR FR7913265A patent/FR2426665A1/fr active Granted
- 1979-05-25 JP JP6407079A patent/JPS54163506A/ja active Granted
-
1988
- 1988-02-25 JP JP63040946A patent/JPS63258435A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH642041A5 (de) | 1984-03-30 |
| JPS54163506A (en) | 1979-12-26 |
| FR2426665B1 (enrdf_load_stackoverflow) | 1983-03-11 |
| FR2426665A1 (fr) | 1979-12-21 |
| NL7904057A (nl) | 1979-11-27 |
| DE2920591A1 (de) | 1979-11-29 |
| US4210611A (en) | 1980-07-01 |
| JPH0154333B2 (enrdf_load_stackoverflow) | 1989-11-17 |
| IT1115235B (it) | 1986-02-03 |
| JPS63258435A (ja) | 1988-10-25 |
| IT7922924A0 (it) | 1979-05-23 |
| JPH0156054B2 (enrdf_load_stackoverflow) | 1989-11-28 |
| DK213479A (da) | 1979-11-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2858248C2 (enrdf_load_stackoverflow) | ||
| DE2742547C2 (enrdf_load_stackoverflow) | ||
| EP0036123B1 (de) | Verfahren zur Herstellung von hochreinen teilfluorierten Äthanen | |
| DE2920591C2 (enrdf_load_stackoverflow) | ||
| DE2708190C2 (de) | Verfahren zur Herstellung von m-Brom-benzotrifluoriden | |
| CH634033A5 (de) | Dihalogenvinyl-verbindungen, verfahren zu deren herstellung sowie deren verwendung zur herstellung von dihalogenvinyl-cyclopropancarbonsaeuren und deren ester. | |
| DE2616681A1 (de) | Verfahren zur reduktiven dehydrohalogenierung von alpha-halogenalkoholen | |
| DE2729911C2 (de) | Verfahren zur Herstellung von α-Chloralkanoylchloriden | |
| DE3710631C2 (enrdf_load_stackoverflow) | ||
| DE2435029B1 (de) | Verfahren zur kontinuierlichen herstellung von monochloralkanan bzw. -cycloalkanen mit mehr als 4 c-atomen im molekuel | |
| EP0048370B1 (de) | Verfahren zur Herstellung von trans-3-(Z-2-Chlor-2-aryl-vinyl)-2,2-dimethyl-cyclopropan-1-carbon-säure-derivaten, neue Zwischenprodukte hierfür, Verfahren zu deren Herstellung und Verwendung von Zwischenprodukten in Schädlingsbekämpfungsmitteln | |
| DE69214914T2 (de) | Verfahren zur Herstellung von 4-Amino-3-Fluorobenzotrifluorid | |
| DE1443388A1 (de) | Verfahren zur Herstellung von Arylfluoriden | |
| DE69301305T2 (de) | Herstellung von Isofluran | |
| DE3925036A1 (de) | Verfahren zur herstellung von fluorierten benzoesaeuren | |
| DE1643589A1 (de) | Verfahren zur Isolierung von Heptafluorisopropyl-2'-jodtetrafluoraethylaether | |
| DE2460821A1 (de) | Verfahren zur herstellung von carbonsaeurefluoriden | |
| EP0103749B1 (de) | Dialkoxymethyl-butyrolactone, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung | |
| DE2240663C3 (de) | Verfahren zur Herstellung von a -Chloraciylsäure | |
| DE2442883A1 (de) | Verfahren zur herstellung von carbonsaeurefluoriden | |
| DE2644594A1 (de) | Fluorsubstitution in 1,1,1-trihalogenalkanen | |
| DE3217029A1 (de) | Verfahren zur herstellung von n-(m-halogenphenyl)-(alpha)-aminosaeureestern | |
| DE69023246T2 (de) | Verfahren zur herstellung von optisch aktiven oder racemischen cyclopropancarbonsäurechloriden. | |
| DE2231438B2 (de) | Verfahren zur Herstellung von 2-Alkyl-2-formyl-1,3-dithiacyclopentanen bzw. 1,3-dithiacyclohexanen | |
| DE3042218A1 (de) | 2,2-dimethylcyclobutanone, und verfahren zu ihrer herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |